Deep Hole Holidays

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    Save up to €185 when you book a flight and hotel together*
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Top hotels in Deep Hole

Quaint Cottages Near Everything on Beach Road

Quaint Cottages Near Everything on Beach Road

Chincoteague
9.4/10 Exceptional! (36 reviews)
"The location was just as described—right in the heart of town yet still peaceful for a relaxing stay. Check in was easy and the host was always easy to reach. The kitchen had most of the basics, though we noticed there wasn’t a pot. The Wi-Fi wasn’t very strong during our stay, and the place could ..."

Reviewed on 12 Aug 2025

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Quaint Cottages Near Everything on Beach Road
An Unfettered View - Beautiful ranch w/ boat dock!

An Unfettered View - Beautiful ranch w/ boat dock!

Chincoteague Island
Fun without sun.
"Even with the wind and rain we had a great time."

Reviewed on 27 Jun 2023

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An Unfettered View - Beautiful ranch w/ boat dock!
Oyster Bay Hideaway on Chincoteague Island!

Oyster Bay Hideaway on Chincoteague Island!

Chincoteague Island
10/10 Exceptional! (9 reviews)
Really nice back view
"I stayed for Pony Swim. It was beautiful overlooking marsh and very convenient"

Reviewed on 5 Aug 2025

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Oyster Bay Hideaway on Chincoteague Island!
See all 740 properties in Deep Hole
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Deep Hole holiday package cost?
You can snap up a holiday package to this destination on Expedia. But how much your holiday to Deep Hole costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Deep Hole?
The off-season is the best time to visit Deep Hole if you're trying to keep costs down. Another tip for finding cheap Deep Hole holiday packages? Try to avoid public holidays and any major events.
How many days is enough for Deep Hole?
Typically, a handful of days is enough to tick off the major attractions during your Deep Hole holiday. However, if you prefer to have time to chill out or take day trips, think about extending your trip.
How to find the best Deep Hole package deals?
Use Expedia's filter tool to find some of the best Deep Hole package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Deep Hole package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package well in advance.
Is it cheaper to book a Deep Hole holiday as a package?
You can enjoy significant savings on your next Deep Hole retreat by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to browse the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Deep Hole?
If you're planning a spur-of-the-moment Deep Hole trip, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Deep Hole?

  1. Choose when to get away: Check your schedule and pack your bags. Your preferred season and the activities on offer will also help you decide when to holiday in Deep Hole.
  2. Calculate your budget: Make sure you have enough money to cover everything from meals and transportation to airfares and activities. Your accommodation will probably be the biggest expense during your trip to Deep Hole.
  3. Work out your trip length: Think about how long you'd like to spend exploring Deep Hole. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your airfare and accommodation: Once you've settled on your dates and duration, lock in the perfect Deep Hole holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.